US2463986A - Derivatives of parabanic acid - Google Patents

Derivatives of parabanic acid Download PDF

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Publication number
US2463986A
US2463986A US569906A US56990644A US2463986A US 2463986 A US2463986 A US 2463986A US 569906 A US569906 A US 569906A US 56990644 A US56990644 A US 56990644A US 2463986 A US2463986 A US 2463986A
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Prior art keywords
derivatives
group
parabanic acid
parabanate
solution
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US569906A
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Kermit D Longley
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QUAKER CHEMICAL PRODUCTS CORP
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QUAKER CHEMICAL PRODUCTS CORP
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Priority to US569906A priority Critical patent/US2463986A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members

Definitions

  • the invention relates to derivatives of parabanic acid and more particularly relates to derivatives of parabanic acid which are suitable for waterproofing textile materials.
  • the invention includes the process of treating textile materials therewith and textile materials so treated.
  • An object of the invention is to provide novel, inexpensive and efficient compositions for imparting durable, water repellent finishes to textile materials.
  • Another object is to provide new and useful compounds.
  • I react a long chain alkyl urea having more than six carbon atoms on the alkyl group with oxalic acid in the presence of a phosphorous halide, or I may react a long chain alkyl urea with an oxalic acid ester in the presence of a sodium alcoholate such as sodium ethylate, sodium methylate, or the like.
  • the long chain parabanate so produced is dispersed in a cold alkali solution. This solution or dispersion forms a textile treating bath. Cloth may be immersed in this solution, passed through a wringer to remove excess solution, and the coated and impregnated cloth then dried at a temperature substantially above room temperature, for example, about 100 C. The heat of the drying decomposes the alkyl parabanate, depositing the aliphatic nucleus on the fabric. There is thus produced on the fabric a highly resistant finish Which is water insoluble and also insoluble in dry cleaning solvents.
  • R in the formula represents an alkyl group having more than six carbon atoms in a straight chain.
  • R. is an aliphatic group having above six carbon atoms and preferably from ten to eighteen carbon atoms, and R is a hydrogen, an aliphatic or aromatic group, or an aliphatic or aromatic group containing a hydrophilic group such as -05, SO3Na, CO.
  • Octadecyl parabanate was made as follows:
  • the finished product is a soft, rather dry paste.
  • Cloth was immersed in this solution, passed through the wringer and dried. A spray test of fifty was obtained.
  • This fabric was then immersed in 10% NH4OH solution three times and dried each time. A spray test of eighty was obtained. This fabric was then washed vigorously with soap, rinsed and again dried. A spray test of seventy-five was obtained.
  • An alkyl parabanate wherein the group attached to one nitrogen atom contains more than nine carbon atoms and the other nitrogen atom is attached to a group selected from the group consisting of hydrogen, an aliphatic group, an aromatic group, an aliphatic group containing a hydrophilic group, andv an aromaticgroup containing a hydrophilic group.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Patented Mar. 8, 1949 DERIVATIVES OF PARABANIC ACID Kermit D. Longley, Philadelphia, Pa., assignor to Quaker Chemical Products Corp., Conshohocken, Pa., a corporation of Pennsylvania No Drawing. Application December 26, 1944, Serial No. 569,906
2 Claims.
The invention relates to derivatives of parabanic acid and more particularly relates to derivatives of parabanic acid which are suitable for waterproofing textile materials. The invention includes the process of treating textile materials therewith and textile materials so treated.
An object of the invention is to provide novel, inexpensive and efficient compositions for imparting durable, water repellent finishes to textile materials.
Another object is to provide new and useful compounds.
Other objects and advantages of the invention will become apparent as the following detailed description progresses.
In accordance with one embodiment of this invention, I react a long chain alkyl urea having more than six carbon atoms on the alkyl group with oxalic acid in the presence of a phosphorous halide, or I may react a long chain alkyl urea with an oxalic acid ester in the presence of a sodium alcoholate such as sodium ethylate, sodium methylate, or the like. The long chain parabanate so produced is dispersed in a cold alkali solution. This solution or dispersion forms a textile treating bath. Cloth may be immersed in this solution, passed through a wringer to remove excess solution, and the coated and impregnated cloth then dried at a temperature substantially above room temperature, for example, about 100 C. The heat of the drying decomposes the alkyl parabanate, depositing the aliphatic nucleus on the fabric. There is thus produced on the fabric a highly resistant finish Which is water insoluble and also insoluble in dry cleaning solvents.
The reaction involved in the above processes is illustrated by the following formula and equations, wherein R in the formula represents an alkyl group having more than six carbon atoms in a straight chain.
deposition on fabric of The preferred parabanates of this invention have the following probable formula:
where R. is an aliphatic group having above six carbon atoms and preferably from ten to eighteen carbon atoms, and R is a hydrogen, an aliphatic or aromatic group, or an aliphatic or aromatic group containing a hydrophilic group such as -05, SO3Na, CO.
The following example is given to illustrate the invention:
Octadecyl parabanate was made as follows:
Forty grams of an ethyl alcoholate containing 2.5 grams of Na metal were placed in a flask fitted with a sealed stirrer and a trap having a. return on it.
To this was added 31 grams of Octadecyl urea and 15 grams of diethyl oxalate. The alcohol was then distilled off and the pasty mass heated to 140 C. and maintained there for one hour. Because of the difficulty of agitation it is not felt that a large amount of the parabanate was obtained. When the heating was discontinued and the temperature had fallen sufficiently the alcohol was returned to the product.
The finished product is a soft, rather dry paste.
A 10% solution of this product (approximately 5% solids) was made. It is not readily dispersible in water alone, but is in ammoniacal solutions.
Cloth was immersed in this solution, passed through the wringer and dried. A spray test of fifty was obtained.
This fabric was then immersed in 10% NH4OH solution three times and dried each time. A spray test of eighty was obtained. This fabric was then washed vigorously with soap, rinsed and again dried. A spray test of seventy-five was obtained.
While I have described certain preferred embodiments of my invention, many modifications thereof may be made without departing from the spirit of the invention; and I do not wish to be limited to the detailed examples, formulas and. proportions of ingredients herein set forth, but desire to avail myself of all changes within the scope of the appended claims.
I claim:
1. An alkyl parabanate wherein the group attached to one nitrogen atom contains more than nine carbon atoms and the other nitrogen atom is attached to a group selected from the group consisting of hydrogen, an aliphatic group, an aromatic group, an aliphatic group containing a hydrophilic group, andv an aromaticgroup containing a hydrophilic group.
2. As a new compound, octadecyl parabanate.
KERMIT D. LONGLEY.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 934,034 Boyeux Sept. 14, 1909 1,861,458 Sobotka June 7, 1932 10 2,186,628 Dickey Jan. 9, 1940 OTHER REFERENCES Monatschefte ffir Chemi'e, vol. 30., page 722. (Copy in Dept. of Agriculture Library, Washington, D. C.)
US569906A 1944-12-26 1944-12-26 Derivatives of parabanic acid Expired - Lifetime US2463986A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3418334A (en) * 1963-10-25 1968-12-24 Monsanto Co Process for the preparation of substituted parabanic acids
US4283547A (en) * 1979-04-25 1981-08-11 Basf Aktiengesellschaft Parabanic acid derivatives
EP0194226A1 (en) * 1985-02-06 1986-09-10 Nippon Zoki Pharmaceutical Co. Ltd. A pharmaceutical composition containing an imidazolidinetrione derivative or pharmaceutically acceptable salt thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US934034A (en) * 1907-01-23 1909-09-14 Joanny Boyeux Method of sizing textile materials.
US1861458A (en) * 1932-06-07 Hakky sobotka
US2186628A (en) * 1937-11-26 1940-01-09 Eastman Kodak Co Yarn conditioning process and composition therefor

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1861458A (en) * 1932-06-07 Hakky sobotka
US934034A (en) * 1907-01-23 1909-09-14 Joanny Boyeux Method of sizing textile materials.
US2186628A (en) * 1937-11-26 1940-01-09 Eastman Kodak Co Yarn conditioning process and composition therefor

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3418334A (en) * 1963-10-25 1968-12-24 Monsanto Co Process for the preparation of substituted parabanic acids
US4283547A (en) * 1979-04-25 1981-08-11 Basf Aktiengesellschaft Parabanic acid derivatives
EP0194226A1 (en) * 1985-02-06 1986-09-10 Nippon Zoki Pharmaceutical Co. Ltd. A pharmaceutical composition containing an imidazolidinetrione derivative or pharmaceutically acceptable salt thereof

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